title: Single-electron-transfer (SET)-induced oxidative biaryl coupling by polyalkoxybenzene-derived diaryliodonium(III) salts.
abstract: Metal-free oxidative C-C coupling by using polyalkoxybenzene-derived diaryliodonium(III) salts as both the oxidant and aryl source has been developed. These salts can induce single-electron-transfer (SET) oxidation to yield electron-rich arenes and subsequently transfer the polyalkoxyphenyl group into in situ generated aromatic radical cations to produce biaryl products. The reaction is promoted by a Lewis acid that activates the iodonium salts. It has been revealed that the reactivity of the salts under acidic conditions is quite different to their known behavior under basic conditions. The reactivity preference of a series of iodonium salts in the SET oxidation and their ligand transfer abilities have been systematically investigated and the results are summarized in this report.
authors.affiliation: College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577 (Japan), Fax: (+81) 77-561-5829.
authors.forename: Nobutaka
authors.initials: N
authors.lastname: Yamaoka
authors.forename: Kohei
authors.initials: K
authors.lastname: Sumida
authors.forename: Itsuki
authors.initials: I
authors.lastname: Itani
authors.forename: Hiroko
authors.initials: H
authors.lastname: Kubo
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Ohnishi
authors.forename: Sho
authors.initials: S
authors.lastname: Sekiguchi
authors.forename: Toshifumi
authors.initials: T
authors.lastname: Dohi
authors.forename: Yasuyuki
authors.initials: Y
authors.lastname: Kita
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D004579:Electron Transport; D004583:Electrons; D008024:Ligands; D009861:Onium Compounds / Q000737:chemistry*; D058451:Oxidative Coupling
chemical_list: D001555:Benzene Derivatives; D008024:Ligands; D009861:Onium Compounds
keywords: biaryls; cross coupling; hypervalent compound; iodine; radical ions; umpolung